Methanol → HCID 15008584, compound

HRID 654852Notes

Reaction equation

HRID 654852 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]([OH:28])([C:18]([CH3:27])([CH3:26])[CH:19](OS(C)(=O)=O)[CH3:20])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1.CO>O1CCCC1.O>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[C:18]([CH3:26])([CH3:27])[CH:19]([CH3:20])[O:28]1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 19886499HCID 19886499, compound

Product 1

HCID 15008584HCID 15008584, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 mg of sodium hydride were added to a solution of 77 mg of this 2-(2,4-difluorophenyl)-3,3-dimethyl-4-(methanesulfonyloxy)-1-(1H-1,2,4-triazol-1-yl)-2-pentanol in 1.5 ml of tetrahydrofuran, whilst ice-cooling and stirring, after which 0.1 ml of methanol was added. After 10 minutes, the reaction mixture was diluted with water and extracted with ethyl acetate. The resulting crude product was purified by column chromatography through silica gel, using a 3:2 by volume mixture of ethyl acetate and hexane as the eluent. The resulting compound was recrystallized from cyclohexane to afford 39 mg of a pure specimen of the title compound, melting at 112°-113° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. customThe resulting crude product was purified by column chromatography through silica gel
  4. additionby volume mixture of ethyl acetate and hexane as the eluent
  5. customThe resulting compound was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-b6ef6fa752b64113a523c194e68d3319
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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